Stereoselective synthesis of some 17beta-dihydrooxazinyl steroids, as novel presumed inhibitors of 17alpha-hydroxylase-C17,20-lyase |
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Authors: | Wölfling János Oravecz Eva Andrea Ondré Dóra Mernyák Erzsébet Schneider Gyula Tóth István Szécsi Mihály Julesz János |
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Institution: | Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary. wolfling@chem.u-szeged.hu |
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Abstract: | 17beta-Dihydrooxazinyl steroids 5a-l and 6a-l were synthetized. The acid-catalyzed reactions of 21-azidomethyl-20-hydroxy- and 21-hydroxymethyl-20-azidosteroids with substituted aromatic aldehydes led to the formation of androst-5-en-3beta-ols substituted in position 17beta with dihydrooxazine residues. The inhibitory effects of these compounds on rat testicular C(17,20)-lyase were investigated with an in vitro radioincubation technique. |
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Keywords: | Heterocyclic steroids Schmidt reaction C17 20-lyase activity |
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